Ammonium Chloride → 5-{2-Iodo-5-[(trimethylsilyl)ethynyl]phenoxy}pyrimidine-2,4-diamine

Participants

Reaction Conditions

Reaction Steps

To a mixture of 5-(2,5-diiodo-4-methoxy-phenoxy)-pyrimidine-2,4-diamine (2.043 g, 4.5 mmol), bis(triphenylphosphine)palladium dichloride (0.316 g, 0.45 mmol) and CuI (43 mg, 0.225 mmol) in 14 mL dry THF was added trimethylsilylacetylene (0.441 g, 4.5 mmol), followed by diisopropylethylamine (7 mL). The reaction mixture was heated at 50° C. under nitrogen atmosphere for 20 hours. The reaction mixture was cooled, poured into saturated aqueous NH4Cl and extracted with dichloromethane. The combined organic layers were washed with water and brine, dried over MgSO4, filtered and concentrated under reduced pressure. The residue was chromatographed on silica (4% MeOH in CH2Cl2 with 0.1% NH4OH) to give 0.350 g of 5-(2,5-Bis-trimethylsilanylethynyl-phenoxy)-pyrimidine-2,4-diamine as a first fraction, and 0.41 g of 5-(2-Iodo-5-trimethylsilanylethynyl-phenoxy)-pyrimidine-2,4-diamine as a second fraction.

Provenance & Evidence